Recent advances in preparation and application of sulfonic acid derivatives bonded to inorganic supports

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Recent advances in preparation and application of sulfonic acid derivatives bonded to inorganic supports Khodabakhsh Niknam1   · Hajar Hashemi1 · Morteza Karimzadeh1 · Dariush Saberi2,3 Received: 23 April 2020 / Accepted: 29 June 2020 © Iranian Chemical Society 2020

Abstract  Heterogeneous acid-catalyzed organic transformations can be classified as one of the most important aspects of catalysis mostly due to its ability in recycling. This review deals with general discussion on the preparation of sulfonic acid derivatives immobilized on inorganic supports such as silica, periodic mesoporous silica, magnetic nanoparticles, metal organic frameworks, KIT-6, ZSM-5, MCM-41, bentonite, boehmite, clay, and other inorganic supports via organic linker. In addition, application of these inorganic supports in the acceleration of organic transformation is discussed one by one. This review aims to provide an overview of the recent developments in the field of heterogenizing homogeneous catalysts with a particular emphasis on the reaction scope and advantages of heterogeneous solid acid catalysts.

This review is dedicated to Professor Hashem Sharghi on the occasion of his 71th birthday. * Khodabakhsh Niknam [email protected] * Morteza Karimzadeh [email protected] 1



Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

2



Fisheries and Aquaculture Department, College of Agriculture and Natural Resources, Persian Gulf University, Bushehr 75169, Iran

3

Marine Chemistry Department, Faculty of Marine Science and Technology, Persian Gulf University, Bushehr 75169, Iran



13

Vol.:(0123456789)



Journal of the Iranian Chemical Society

Graphic abstract NHSO3H

HO3SHN

O

HO3SHN

O

Cl ) O n

(

HO3S

HSO4

H2N H N

O

HO

HO3SN

NH

2

N an o Magnetic Nanoparticles -A l 2O lit e1

lic a

O

N HN Cl HO S 3

3

HN SO3H SO3H

F F F F3C SO3H

Zirconium phosphonate

Silica HO Cl

HO3S

HO3S

P

MC

3

lO

NH N H HN F F

O O O p O SO3H Cl HO3SN SO3H

F

NH2

SO3H

SO3H

M -4

PM

HO3S

N

NSO3H

N

1

Si

Na cli nono Ze Bentonite pt oli ilo t lite

N

HSO4

CO2H O

MOF

ZS

N

Ti O

-6

N

O

2

Cl N

HO3S

KIT

N

Hydroxyapatite

N

O ic a

15

Cl

P P

S il

e lit eo

HO3S

HO3SN

O

no

-Z OR

HO3S

F

FF

a ilic

M

F 3C

p

sS

SO3H

O

ASB

HO3S

so Me

u oro

Na

SO3H

γ -A

S

SO3H

-5

S

NSO3H

M

HO SO HO3S O 3

F

F

O

NHSO3H

F

F F

SO3H SO3H

SO2H

SO3H

Keywords  Magnetic nanoparticle · SBA-15 · MCM-41 · Sulfonic acid · Sulfamic acid · Periodic mesostructured organosilica

Introduction Many of the organic reactions can be performed in the presence of acidic catalysts. These catalysts generally are classified into two groups: homogeneous and heterogeneous acidic catalysts. A major source of waste in the chemical industry is derived from the widespread use of mineral acids as homogeneous catalysts. These acids such as H ­ 2SO4, HF, H ­ 3PO4, ­AlCl3, and B ­ F3 are hazardous in handling and damaging the plant and environment through their corrosiveness, and